Selective hetero-trisfunctionalization of the large rim of a biomimetic calix[6]arene using host-guest chemistry as a synthetic tool.
A calix[6]arene has been selectively functionalized by three different groups at the large rim. The strategy relies on the hostguest recognition chemistry of a biomimetic metal complex at the small rim (so-called "funnel complex") and the Huisgen cycloaddition. The intramolecular thermal reaction proceeds with a high efficiency, chemio- and regioselectivity, allowing the monofunctionalization of one aromatic unit among three. Thanks to the high yield and selectivity of the reaction, it can be applied successively twice on the same compound, which opens the route for inherently chiral calix[6]arenes. This methodology not only is of wide potential for obtaining and exploiting calix[6]arenes that are dissymmetrized at the large rim, but also stands as an exemplary strategy for the selective appending of a functional group on a host platform.
Colasson
Benoit
B
Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, CNRS UMR 8601 Université Paris Descartes, 45 rue des Saints Pères, 75006 Paris, France.
Reinaud
Olivia
O
D040761:Biomimetic Materials / Q000138:chemical synthesis* / Q000737:chemistry; D047250:Calixarenes / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D010636:Phenols / Q000138:chemical synthesis* / Q000737:chemistry
D010636:Phenols; C476540:calix(6)arene; D047250:Calixarenes